Director of Regulatory Operations, 2 Hour Learning (Remote) - $200,000/year USD

A law degree is not required—but Legal will call you when they're out of answers. This role centers on permission, not policy. You will secure the regulatory clearances that enable new schools to open, owning every step from entity filings through license approvals to edge-case exemptions. Your work will unlock legal operation in all 50 states. AI tools such as a RAG Bot will help you produce jurisdiction-specific memos and accelerate filings, but you remain the critical human layer: identifying ambiguity, flagging red and yellow risks, escalating obstacles, and driving decisions forward. As others deliberate on strategy, you deliver outcomes. You will test and optimize intelligent workflows, maintain live dashboards, and ensure nothing falls through the cracks. The systems you create will serve as the definitive reference for legal, operations, and executive leadership. This is not a support function. It is a frontline builder position demanding speed, ownership, and practical regulatory expertise. You will not simply maintain operations—you will construct the infrastructure. What You Will Be Doing

• Produce AI-enhanced legal research memos that convert fragmented regulatory environments into actionable go/no-go guidance — delivered within 48 hours.
• Assemble and file state-specific submission packages — exemption letters, licensing applications, and entity documentation — ensuring no dependencies are overlooked.
• Monitor all approvals in real time via dashboards you design (e.g., Airtable, Klair, Retool), escalating roadblocks and setting alerts ahead of deadlines.
• Resolve edge-case denials, address cross-jurisdictional conflicts, and own the final compliance mile — from filing through final approval sign-off.
• Iteratively improve the AI and automation infrastructure by testing results, engineering workflows, and deploying updates that increase both accuracy and velocity.

What You Won’t Be Doing

• Waiting for legal or product teams to provide answers — you are expected to discover them or architect the system that does.
• Relying on static checklists or legacy compliance frameworks — this position is fluid, AI-enabled, and in continuous evolution.
• Handling backend corrections or repairing incomplete filings — your submissions are accurate, thorough, and approved ahead of schedule, not in retrospect.
• Communicating status through email chains — all stakeholders access the same live, audit-ready tracking system you maintain.
• Treating compliance as a theoretical task — you deliver outcomes that directly affect launch timelines and public exposure.

Director Of Regulatory Operations Key Responsibilities Obtain and sustain the legal authorizations required for 2 Hour Learning to launch and operate schools nationwide — through the design, ownership, and execution of scalable, technology-driven compliance frameworks. Basic Requirements

• Based in the U.S. and authorized to work without sponsorship
• Willing to travel 50–75% of the time across U.S. jurisdictions
• 5+ years in compliance, permitting, legal ops, or multi-state operations
• Demonstrated track record of owning outcomes in fast-moving, ambiguous domains
• Daily user of AI tools (e.g., ChatGPT, Claude, Perplexity) and low-code platforms (e.g., Retool, Airtable, Klair, Zapier)
• High-speed executor — delivers filings or research within 48 hours, closes loops without prompting
• Precision communicator — writes decision-ready memos, crisp summaries, and audit-proof trackers

Nice-to-have Requirements

• Familiarity with AI prompt engineering, regulatory databases, or designing workflows in compliance-heavy environments
• Track record of proactively spotting and solving edge-case regulatory blockers

About 2 Hour Learning Education is broken, but 2 Hour Learning is proving it doesn’t have to be. They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day. With students consistently ranking in the top 1-2% nationally and the top 20% achieving an astonishing 6.5x growth, they’re proving that smarter learning is possible. At 2 Hour Learning, it’s talent and performance that matter. They offer a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can be a part of fixing a broken school system. 2 Hour Learning is reprogramming learning for the AI era.Here’s How They’re Fixing It. There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you! Working with us This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic. Crossover Job Code: LJ-5678-US-Philadel-DirectorofRegu